Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 6.SE, Problem 25EDRM
When isopropylidenecyclohexane is treated with strong acid at room temperature, isomerization occurs by the mechanism shown below to yield 1-isopropylcyclohexene:
At equilibrium, the product mixture contains about 30% isopropyl-idenecyclohexane and about 70% 1-isopropylcyclohexene.
(a) What is an approximate value of Keq for the reaction?
(b) Since the reaction occurs slowly at room temperature, what is its approximate ∆G‡?
(c) Draw an energy diagram for the reaction.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Arrange the alkenes in each set in order of increasing rate of reaction with HI and
explain the basis for your ranking. Draw the structural formula of the major product
formed in each case.
(a)
and
(b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3
A tautometric keto (A) – enol(B) equilibrium may be formulated as follows
(A) (B)
CH3 – COH ß-----------àCH2 – CHOH
Given the following bond energies:
C – H = 435kJ mol-1
C – C = 368
C==C = 610
C – O = 357 kJmol-1
C==O = 748 kJmol-1
O – H = 462 kJ mol-1
Calculate the enthalpy change in going from Keto form (A) to the enol form (B)
Predict the products of the following acid-base reactions. If the equilibrium would not
result in the formation of appreciable amounts of products, you should so indicate. In
each case label the stronger acid, the stronger base, the weaker acid, and the weaker base:
(a) CH3CH=CH2 + NANH2
(d) CH3C=C: + CH;CH2OH →
(e) CH3C=C:- + NH¾CI –
|
(b) CH;C=CH + NaNH2
(c) CH3CH2CH3 + NANH2 →
|
HAS
Chapter 6 Solutions
Organic Chemistry
Ch. 6.1 - Prob. 1PCh. 6.3 - Prob. 2PCh. 6.3 - Using curved fishhook arrows, propose a mechanism...Ch. 6.4 - Prob. 4PCh. 6.4 - An electrostatic potential map of boron...Ch. 6.5 - What product would you expect from reaction of...Ch. 6.5 - Reaction of HBr with 2-methylpropene yields...Ch. 6.6 - Prob. 8PCh. 6.6 - Predict the products of the following polar...Ch. 6.7 - Which reaction is more energetically favored, one...
Ch. 6.7 - Prob. 11PCh. 6.9 - Which reaction is faster, one with ∆G‡ = +45...Ch. 6.10 - Prob. 13PCh. 6.SE - Prob. 14VCCh. 6.SE - Prob. 15VCCh. 6.SE - Prob. 16VCCh. 6.SE - Look at the following energy diagram: (a) Is...Ch. 6.SE - Look at the following energy diagram for an...Ch. 6.SE - What is the difference between a transition state...Ch. 6.SE - Prob. 20EDRMCh. 6.SE - Prob. 21EDRMCh. 6.SE - Draw an energy diagram for a two-step exergonic...Ch. 6.SE - Draw an energy diagram for a reaction with keq =...Ch. 6.SE - The addition of water to ethylene to yield ethanol...Ch. 6.SE - When isopropylidenecyclohexane is treated with...Ch. 6.SE - Prob. 26EDRMCh. 6.SE - Draw the electron-pushing mechanism for each...Ch. 6.SE - Draw the complete mechanism for each polar...Ch. 6.SE - Prob. 29EDRMCh. 6.SE - Identify the functional groups in the following...Ch. 6.SE - Identify the following reactions as additions,...Ch. 6.SE - Identify the likely electrophilic and nucleophilic...Ch. 6.SE - For each reaction below identify the electrophile...Ch. 6.SE - Prob. 34APCh. 6.SE - Follow the flow of electrons indicated by the...Ch. 6.SE - Prob. 36APCh. 6.SE - Prob. 37APCh. 6.SE - Despite the limitations of radical chlorination of...Ch. 6.SE - Prob. 39APCh. 6.SE - Answer question 6-39 taking all stereoisomers into...Ch. 6.SE - Prob. 41APCh. 6.SE - Prob. 42APCh. 6.SE - Prob. 43APCh. 6.SE - The reaction of hydroxide ion with chloromethane...Ch. 6.SE - Prob. 45APCh. 6.SE - Ammonia reacts with acetyl chloride (CH3COCl) to...Ch. 6.SE - The naturally occurring molecule α-terpineol is...Ch. 6.SE - Prob. 48APCh. 6.SE - Prob. 49APCh. 6.SE - Draw the structures of the two carbocation...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardFollowing is a balanced equation for bromination of toluene.(a) Using the values for bond dissociation enthalpies given in Appendix 3,calculate ∆H0for this reaction.(b) Propose a pair of chain propagation steps and show that they add up to theobserved reaction.(c) Calculate ∆H0for each chain propagation step.(d) Which propagation step is rate-determininarrow_forwardPredict which member of each group is most soluble in water, and explain the reasons for your predictions.(a) butan-1-ol, pentan-1-ol, or propan-2-ol(b) chlorocyclohexane, cyclohexanol, or cyclohexane-1,2-diol(c) phenol, cyclohexanol, or 4-methylcyclohexanolarrow_forward
- Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octetarrow_forwardGive the structure of the product formed when each of the following alkenes reacts with bromine in water: (a) 2-Methyl-1-butene (c) 3-Methyl-1-butene (b) 2-Methyl-2-butene (d) 1-Methylcyclopentenearrow_forwardIf a catalyst could be found that would establish an equilibrium between 1,2-butadiene and 2-butyne, what would be the ratio of the more stable isomer to the less stable isomer at 25°C? CH,=C=CHCH, CH,C=CCH, AG° = -16.7 kJ (-4.0 kcal)/molarrow_forward
- (a) rate at which the following alcohols undergo dehydration to form alkenes in sulfuric acid OH OH OH (b) rate at which the following alkenes undergo addition with HBr to form an alkyl halidearrow_forwardGive an IUPAC and common name for each of the following naturally occurring carboxylic acids: (a) CH3CH(OH)CO2H (lactic acid); (b) HOCH2CH2C(OH)(CH3)CH2CO2H (mevalonic acid).arrow_forward(i) State reagents G and J. (ii) Draw the structural formula for compounds D, E and H.arrow_forward
- Please give the main substitution product for each of the following reactions, and indicate the dominant mechanism: (a) 1-bromopropane + NaOCH3 → (b) 3-bromo-3-methylpentane + NaOC2H5 →arrow_forwardSome of the most useful compounds for organic synthesisare Grignard reagents (general formula R-MgX, where X is ahalogen), which are made by combining an alkyl halide, R-X,with Mg. They are used to change the carbon skeleton of a start-ing carbonyl compound in a reaction similar to that with R-Li:.(a) What is the product, after a final step with water, of thereaction between ethanal and the Grignard reagent of bromo-benzene? (b) What is the product, after a final step with water, ofthe reaction between 2-butanone and the Grignard reagent of2-bromopropane? (c) There are often two (or more) combina-tions of Grignard reagent and carbonyl compound that will givethe same product. Choose another pair of reactants to give theproduct in (a). (d) What carbonyl compound must react with aGrignard reagent to yield a product with the -OH group at theendof the carbon chain? (e) What Grignard reagent and carbonylcompound would you use to prepare 2-methyl-2-butanol?arrow_forwardThe reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an SN2mechanism. What happens to the rate of this reaction under the following conditions?(a) The concentration of NaOH is doubled.(b) The concentrations of both NaOH and 1-bromopropane are doubled.(c) The volume of the solution in which the reaction is carried out is doubled.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY